Does reality always win?

The answer may be yes, but sometimes not in time for the people involved. But that's no reason for despair.

Freedom implies the ability to make mistakes; it may even imply the necessity of them. Well might the perfect being exclaim: “not till now have I understood the tale of your people and their fall. … For if this is indeed, as the Eldar say, the gift of the One to Men, it is bitter to receive.” Bitter indeed; for freedom is humanity’s curse and greatest gift, the ground of both fall and redemption. It is our common fate and our staircase to the stars.